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2012 | 10 | 5 | 1600-1608
Tytuł artykułu

Role of water in determining organic reactivity in aqueous binary solvents

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Kinetic data for organic reactions in various binary water-organic solvent mixtures were collected and quantitatively analysed in terms of linear-free-energy relationships by using tert-butyl chloride (2-chloro-2-methylpropane) solvolysis as the reference system. Linear similarity plots for these kinetic data were determined for solvent systems ranging from pure water mixtures up to considerable amount of cosolvent, and 161 similarity coefficients were calculated from slopes of these plots. The existence of these linear plots demonstrated that the solvent effects are of some common nature in all analysed reaction mixtures independent of the reaction type and the cosolvent used. Therefore it was concluded that the observed effects could be connected to the specific solvating properties of water, which govern reactivity even in significant dilution of water by an organic cosolvent. This conclusion was supported by the linear interrelationship between the slopes of similarity plots of different reactions, and hydrophobicity parameters log P of the reacting compounds. The relative solvent effects observed in binary water-organic solvent mixtures were for the first time directly related to the structure of reacting compounds. [...]
Wydawca

Czasopismo
Rocznik
Tom
10
Numer
5
Strony
1600-1608
Opis fizyczny
Daty
wydano
2012-10-01
online
2012-07-21
Twórcy
autor
  • Institute of Chemistry, University of Tartu, 50411, Tartu, Estonia, siim.salmar@ut.ee
autor
  • Institute of Chemistry, University of Tartu, 50411, Tartu, Estonia
autor
  • Institute of Chemistry, University of Tartu, 50411, Tartu, Estonia
  • Institute of Chemistry, University of Tartu, 50411, Tartu, Estonia
Bibliografia
  • [1] R. Breslow, In: M. Lindström (Ed.), Organic Reactions in Water (Blackwell Publishers, Oxford, 2007) Chapter 1
  • [2] T.J. Mason, P. Cintas, In: J. Clark, D. Macquarrie (Eds), Handbook of Green Chemistry (Blackwell Publishers, Oxford, 2000)
  • [3] F. Franks (Ed.), Water: a Comprehensive Treatise (Plenum Press, New York, 1972–1982) Vols. 1–7
  • [4] C. Reichardt, T. Welyon, Solvents and Solvent Effects in Organic Chemistry, 4th edition (Wiley-VCH, Weinheim, 2011)
  • [5] J.B.F.N. Engberts, In: F. Franks (Ed.) Water: a Comprehensive Treatise (Plenum Press, New York, 1979) Vol. 6, Chapter 4
  • [6] M.J. Blandamer, J. Burgess, J.B.F.N. Engberts, P. Warrick Jn., J. Mol. Liq. 52, 15 (1992) http://dx.doi.org/10.1016/0167-7322(92)80094-X[Crossref]
  • [7] D.N. Shin, J.W. Wijnen, J.B.F.N. Engberts, A. Wakisaka, J. Phys. Chem. B 106, 6014 (2002) http://dx.doi.org/10.1021/jp020414+[Crossref]
  • [8] O.A. El Seoud, Pure Appl. Chem. 81, 697, (2009) http://dx.doi.org/10.1351/PAC-CON-08-09-27[Crossref]
  • [9] P.L. Silva, M.A.S. Trassi, C.T. Martins, O.A. El Seoud, J. Phys. Chem. B 113, 9512 (2009) http://dx.doi.org/10.1021/jp902272g[Crossref]
  • [10] W. Blokzijl, J.B.F.N. Engberts, Angew. Chem. 105, 1610 (1993) http://dx.doi.org/10.1002/ange.1761051104[Crossref]
  • [11] W. Blokzijl, J.B.F.N. Engberts, Angew. Chem. Int. Ed. Engl. 32, 1545 (1993) http://dx.doi.org/10.1002/anie.199315451[Crossref]
  • [12] S. Otto, J.B.F.N. Engberts, Org. Biomol. Chem. 1, 2809 (2003) http://dx.doi.org/10.1039/b305672d[Crossref]
  • [13] C. Tanford, The Hydrophobic Effect, 2nd edition (Wiley, New York, 1980)
  • [14] N.T. Southall, K.A. Dill, A.D.J. Haymet, J. Phys. Chem. B 106, 521 (2002) http://dx.doi.org/10.1021/jp015514e[Crossref]
  • [15] U.M. Lindström, Chem. Rev. 102, 2751 (2002) http://dx.doi.org/10.1021/cr010122p[Crossref]
  • [16] C. Li, Chem. Rev. 105, 3095 (2005) http://dx.doi.org/10.1021/cr030009u[Crossref]
  • [17] C.T. Martins, M.S. Lima, O.A. El Seoud, J. Org. Chem. 71, 9068 (2006) http://dx.doi.org/10.1021/jo061533e[Crossref]
  • [18] K.A. Connors, In: G. Wypych (Ed.), Handbook of Solvents (ChemTec Publishing, Toronto, 2001) 281
  • [19] W. Blokzijl, J.B.F.N. Engberts, J. Jager, M.J. Blandamer, J. Phys. Chem. 91, 6022 (1987) http://dx.doi.org/10.1021/j100307a041[Crossref]
  • [20] T. Rispens, C. Caballeiro-Lago, J.B.F.N. Engberts, Org. Biomol. Chem. 3, 597 (2005) http://dx.doi.org/10.1039/b414593c[Crossref]
  • [21] T. Rispens, J.B.F.N. Engberts, J. Phys. Org. Chem. 18, 725 (2005) http://dx.doi.org/10.1002/poc.926[Crossref]
  • [22] T.W. Bentley, H.C. Harris, Z.H. Ryu, G.T. Lim, D.D. Sung, S.R. Szajda, J. Org. Chem. 70, 8963 (2005) http://dx.doi.org/10.1021/jo0514366[Crossref]
  • [23] T.W. Bentley, M.S. Garley, J. Phys. Org. Chem. 19, 341 (2006) http://dx.doi.org/10.1002/poc.1084[Crossref]
  • [24] M.J. D’Souza, M.J. McAneny, D.N. Kevill, J.B. Kyong, S.H. Choi, Beilstein J. Org. Chem. 7, 543 (2011), and references therein. http://dx.doi.org/10.3762/bjoc.7.62[Crossref]
  • [25] D.N. Kevill, K.H. Park, H.J. Koh, J. Phys. Org. Chem. 24, 378 (2011) http://dx.doi.org/10.1002/poc.1767[Crossref]
  • [26] K.H. Park, D.N. Kevill, J. Phys. Org. Chem. 25, 267 (2011) http://dx.doi.org/10.1002/poc.1906[Crossref]
  • [27] R. Breslow, J. Phys. Org. Chem. 19, 813 (2006) http://dx.doi.org/10.1002/poc.1037[Crossref]
  • [28] A. Tuulmets, S. Salmar, H. Hagu, J. Phys. Chem. B 107, 12891 (2003) http://dx.doi.org/10.1021/jp035714l[Crossref]
  • [29] A. Tuulmets, H. Hagu, S. Salmar, G. Cravotto, J. Järv, J. Phys. Chem. B 111, 3133 (2007) http://dx.doi.org/10.1021/jp0682199[Crossref]
  • [30] A. Tuulmets, J. Järv, S. Salmar, G. Cravotto, J. Phys. Org. Chem. 21, 1002 (2008) http://dx.doi.org/10.1002/poc.1415[Crossref]
  • [31] A. Tuulmets, S. Salmar, J. Järv, Sonochemistry in Water Organic Solutions (Nova Science Publishers, New York, 2010)
  • [32] A. Tuulmets, J. Järv, T. Tenno, S. Salmar, J. Mol. Liq. 148, 94 (2009) http://dx.doi.org/10.1016/j.molliq.2009.06.008[Crossref]
  • [33] A. Williams, Free Energy Relationships in Organic and Bio-organic Chemistry, (RSC, Cambridge, 2003)
  • [34] E. Grunwald, S. Winstein, J. Am. Chem. Soc. 70, 846 (1948) http://dx.doi.org/10.1021/ja01182a117[Crossref]
  • [35] R.I. Zalewski, T.M. Krygowski, J. Shorter, Similarity Models in Organic Chemistry, Biochemistry and Related Fields (Elsevier, New York, 1991)
  • [36] A.H. Fainberg, S. Winstein, J. Am. Chem. Soc. 78, 2770 (1956) http://dx.doi.org/10.1021/ja01593a033[Crossref]
  • [37] R.E. Robertson, Can. J. Chem. 50, 1353 (1972) http://dx.doi.org/10.1139/v72-212[Crossref]
  • [38] K. Heinonen, E. Tommila, Suomen Kem. B38, 9 (1965)
  • [39] S. Winstein, E. Grunwald, H.W. Jones, J. Am. Chem. Soc. 73, 2700 (1951) http://dx.doi.org/10.1021/ja01150a078[Crossref]
  • [40] D.N. Kevill, M.J. D’souza, J. Chem. Res. 61–66 (2008)
  • [41] E. Tommila, A. Koivisto, J.P. Lyyra, K. Antell, S. Heimo, Ann Acad. Sci. Fennicae A11, Nr. 47 (1952)
  • [42] A.H. Fainberg, S. Winstein, J. Am. Chem. Soc. 79, 1602 (1957) http://dx.doi.org/10.1021/ja01564a022[Crossref]
  • [43] D.N. Kevill, M.J. D’souza, J. Org. Chem. 69, 7044 (2004) http://dx.doi.org/10.1021/jo0492259[Crossref]
  • [44] M. Harati, M.R. Gholami, Int. J. Chem. Kinetics 37(2), 90 (2005) http://dx.doi.org/10.1002/kin.20041[Crossref]
  • [45] A.A. Sosunov, A.P. Kilimov, V.V. Smirnov, Zh. Obch. Khimii 40, 2688 (1970) (in Russian)
  • [46] Y. Marcus, Solvent Mixtures-Properties and Selective Solvation (M. Dekker, New York, Basel, 2002)
  • [47] K. Egashira, N. Nishi, J. Phys. Chem. B 102, 4054 (1998) http://dx.doi.org/10.1021/jp9806359[Crossref]
  • [48] T. Takamuku, T. Yamaguchi, M. Asato, M. Matsumoto, N. Nishi, Z. Naturforsch., Part A 55a, 513 (2000)
  • [49] A. Wakasaka, S. Komatsu, Y. Usui, J. Mol. Liq. 90, 175 (2001) http://dx.doi.org/10.1016/S0167-7322(01)00120-9[Crossref]
  • [50] S. Dixit, J. Crain, W.C.K. Poon, J.L. Finney, A.K. Soper, Nature 416, 829 (2002) http://dx.doi.org/10.1038/416829a[Crossref]
  • [51] Y. Liu, X. Luo, Z. Shen, J. Lu, X. Ni, Optical Rev. 13, 303 (2006) http://dx.doi.org/10.1007/s10043-006-0303-3[Crossref]
  • [52] A. Wakisaka, K. Matsura, J. Mol. Liq. 129, 25 (2006) http://dx.doi.org/10.1016/j.molliq.2006.08.010[Crossref]
  • [53] N.P. Hu, D. Wu, K. Cross, S. Burikov, T. Dolenko, S. Patsaeva, D.W. Schaefer, J. Agric. Food Chem. 57, 7394 (2010) http://dx.doi.org/10.1021/jf100609c[Crossref]
  • [54] A.H. Fainberg, S. Winstein, J. Am. Chem. Soc. 79, 1602 (1957) http://dx.doi.org/10.1021/ja01564a022[Crossref]
  • [55] A.H. Fainberg, S. Winstein, J. Am. Chem. Soc. 79, 1608 (1957) http://dx.doi.org/10.1021/ja01564a023[Crossref]
  • [56] T.W. Bentley, I.S. Koo, S.J. Norman, J. Org. Chem. 56, 1604 (1991) http://dx.doi.org/10.1021/jo00004a048[Crossref]
  • [57] T.W. Bentley, I.S. Koo, H. Choi, G. Llewellyn, J. Phys. Org. Chem. 21, 251 (2008) http://dx.doi.org/10.1002/poc.1308[Crossref]
  • [58] A. Leo, C. Hansch, D. Elkins, Chem. Rev. 71, 525 (1971) http://dx.doi.org/10.1021/cr60274a001[Crossref]
  • [59] C. Hansch, Acc. Chem. Res. 2, 232 (1969) http://dx.doi.org/10.1021/ar50020a002[Crossref]
  • [60] ACD/ChemSketch Freeware (Advanced Chemistry Development, Inc., Canada, 2010)
  • [61] M.H. Abraham, J.C. Dearden, G.M. Bresnen, J. Phys. Org. Chem. 19, 242 (2006) http://dx.doi.org/10.1002/poc.1027[Crossref]
  • [62] P. Sikk, A. Aaviksaar, A. Abduvahhabov, Eesti NSV Tead. Akad. Toim., Keem., Geol. 26(3), 242 (1977) (in Russian)
  • [63] K.A. Connors, M.J. Mulski, A. Paulson, J. Org. Chem. 57, 1794 (1992) http://dx.doi.org/10.1021/jo00032a036[Crossref]
  • [64] J.M. LePree, M.J. Mulski, K.A. Connors, J. Chem. Soc. Perkin Trans. 2 1491 (1994) [Crossref]
  • [65] N.J. Buurma, L. Pastorello, M.J. Blandamer, J.B.F.N. Engberts, J. Am. Chem. Soc. 123, 11848 (2001) http://dx.doi.org/10.1021/ja010617w[Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-012-0080-8
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